Methyl chloroformate → HCID 20483501, compound

HRID 1764338Notes

Reaction equation

HRID 1764338 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[NH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH:17]([OH:23])[CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])=[N:13][CH:14]=1>C(O)(C)C.O>[CH:20]([NH:19][CH2:18][CH:17]([OH:23])[CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][NH:6][C:3]([O:2][CH3:1])=[O:4])=[CH:14][N:13]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 20483409HCID 20483409, compound

Product 1

HCID 20483501HCID 20483501, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5.4 ml of chloroformic acid methyl ester are added dropwise, whilst stirring, to 12.4 g of 5-(2'-aminoethyl)-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyridine, dissolved in a mixture of 45 ml of isopropanol and 45 ml of water, at a temperature of 20°-35° C., with cooling by means of ice water, if necessary. The reaction mixture is stirred further for one hour at room temperature and is evaporated in vacuo, and the evaporation residue is dissolved in approx. 30 ml of water. This solution is extracted with 20 ml of ethyl acetate and the acid aqueous phase is rendered alkaline with concentrated sodium hydroxide solution. The oil which precipitates is extracted with dichloromethane. After drying the solution over magnesium sulphate and evaporating off the solvent, 2-(3'-isopropylamino-2'-hydroxy-propoxy)-5-(2'-methoxycarbonylaminoethyl)-pyridine is obtained, melting at 97°-99° C. after recrystallisation from a little butanone.

Workup

  1. customis evaporated in vacuo
  2. dissolutionthe evaporation residue is dissolved in approx. 30 ml of water
  3. extractionThis solution is extracted with 20 ml of ethyl acetate
  4. customThe oil which precipitates
  5. extractionis extracted with dichloromethane
  6. dry with materialAfter drying the solution over magnesium sulphate
  7. customevaporating off the solvent

Sources & evidence

ORD record
ord-0b6071d161de4c8ab8624897e3efe072
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

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